1995 – Shawn Michaels
Michaels became the first participant to win a Rumble from the #1 position.
Time lasted: 38:41
Eliminations: 8
Eliminated by: WINNER
1996 – Hunter Hearst Helmsley
Helmsley lost a match via DQ to Duke Droese on the pre-show that meant he had to enter first while Droese entered at #30.
Time lasted: 48:04
Eliminations: 1
Eliminated by: Diesel
1997 – Crush
Crush and the rest of the Nation of Domination were in Faarooq’s corner for his match against Ahmed Johnson – who entered the Rumble at #2 – earlier in the night.
Time lasted: 06:17
Eliminations: 0
Eliminated by: Phineas Goddwin
1998 – Cactus Jack
Mick Foley became the only person to enter a Rumble with three different personas in the ’98 Rumble. He entered as Cactus Jack (#1), Mankind (#16), and Dude Love (#28).
Time lasted: 09:21
Eliminations: 1
Eliminated by: Chainsaw Charlie
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